2-trimethylsilylethyl (Z)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-2-enoate | 331952-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-trimethylsilylethyl (Z)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-2-enoate
• CAS: 331952-13-7
• 化学式: C₃₀H₅₀N₂O₁₃Si
• 分子量: 674.818
• InChiKey: DNDHPMKFHXBPLO-RHAZSZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  46
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl (Z)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-2-enoate 在 1,2-bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、344.75 kPa 条件下， 以99%的产率得到2-trimethylsilylethyl (2S)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  Pursuit of Optimal Carbohydrate-Based Anticancer Vaccines:  Preparation of a Multiantigenic Unimolecular Glycopeptide Containing the Tn, MBr1, and Lewis^y Antigens

  摘要：

  A novel preparation of nonnatural glycoamino acids starting from n-pentenyl glycosides is described. The approach involves a Horner-Emmons olefination with a suitably protected glycine-derived phosphonate, followed by catalytic asymmetric hydrogenation, which proceeds with excellent diastereomeric selectivity. The synthetic methodology was useful for the preparation of glycoamino acids containing the Tn antigen, the MBr1 antigen (Globo-H), the Le(y) antigen, and lactose. These glycoamino acids can also serve as units for peptide synthesis. The synthesis of polyvalent glycopeptides containing three different antitumor antigens is described (28 and 29), and these have been prepared for conjugation to carrier protein in order to access the immunogenicity for turner immunotherapy applications.

  DOI：

  10.1021/ja002779i
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose 在 三氟甲磺酸三甲基硅酯 吡啶 、 potassium carbonate 、 臭氧 、 四甲基胍 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.25h， 生成 2-trimethylsilylethyl (Z)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-2-enoate
  参考文献：
  名称：

  Pursuit of Optimal Carbohydrate-Based Anticancer Vaccines:  Preparation of a Multiantigenic Unimolecular Glycopeptide Containing the Tn, MBr1, and Lewis^y Antigens

  摘要：

  A novel preparation of nonnatural glycoamino acids starting from n-pentenyl glycosides is described. The approach involves a Horner-Emmons olefination with a suitably protected glycine-derived phosphonate, followed by catalytic asymmetric hydrogenation, which proceeds with excellent diastereomeric selectivity. The synthetic methodology was useful for the preparation of glycoamino acids containing the Tn antigen, the MBr1 antigen (Globo-H), the Le(y) antigen, and lactose. These glycoamino acids can also serve as units for peptide synthesis. The synthesis of polyvalent glycopeptides containing three different antitumor antigens is described (28 and 29), and these have been prepared for conjugation to carrier protein in order to access the immunogenicity for turner immunotherapy applications.

  DOI：

  10.1021/ja002779i